NP-MRD: Showing NP-Card for 18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone (NP0206828)

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Record Information

Version

2.0

Created at

2022-09-05 03:13:28 UTC

Updated at

2022-09-05 03:13:28 UTC

NP-MRD ID

NP0206828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone

Description

18-Chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]Hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. 18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone is found in Gilmaniella humicola. 18-Chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]Hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514142D          

 37 43  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161514142D          

 37 43  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0206828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)OCC34C2=C1C(=O)CC3(O)C1C(O)C42COC(=O)C3=C(O)C(Cl)=C(C)C(C1=O)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C26H19ClO10/c1-7-3-9(28)13-16-11(7)10(29)4-26(35)17-19(30)12-8(2)18(27)20(31)14-15(12)24(21(17)32,5-36-23(14)34)25(16,26)6-37-22(13)33/h3,17,21,28,31-32,35H,4-6H2,1-2H3

> <INCHI_KEY>
YNFQXIDQMWVTNH-UHFFFAOYSA-N

> <FORMULA>
C26H19ClO10

> <MOLECULAR_WEIGHT>
526.88

> <EXACT_MASS>
526.0666745

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
48.277185575505754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16(25),17,19-hexaene-5,11,15,21-tetrone

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.3445947903333333

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.061614085372645

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.608679040215831

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2919213258129343

> <JCHEM_POLAR_SURFACE_AREA>
167.66

> <JCHEM_REFRACTIVITY>
126.32349999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16(25),17,19-hexaene-5,11,15,21-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      12.239   5.761   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.753   4.300   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.740   3.126   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.226   1.671   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.221   0.496   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.675   1.396   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.337  -0.104   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.477  -1.140   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       8.887  -0.579   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.760   0.479   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.809   2.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.534   2.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.238   3.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.443   5.248   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.152   6.616   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.947   5.150   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494   3.651   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.646   4.936   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.168   3.798   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.460   2.095   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.896   1.539   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.669   1.478   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.486  -0.097   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.190  -0.937   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.813  -0.236   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.536  -1.097   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.680   1.297   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.233   1.952   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.015   1.049   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.068   3.493   0.000  0.00  0.00           C+0
HETATM   31 Cl   UNK     0      -0.336   4.125   0.000  0.00  0.00          Cl+0
HETATM   32  C   UNK     0       2.324   4.386   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.205   5.921   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.733   3.681   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.915   4.616   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.845   6.155   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.004   2.111   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17   22                                             
CONECT   12   11    6   13                                                  
CONECT   13   12    2   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20   35                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   11   23   37                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   37                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   37                                                  
CONECT   35   34   19   36                                                  
CONECT   36   35                                                            
CONECT   37   34   22   27                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₁₉ClO₁₀

Average Mass

526.8800 Da

Monoisotopic Mass

526.06667 Da

IUPAC Name

18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16(25),17,19-hexaene-5,11,15,21-tetrone

Traditional Name

18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16(25),17,19-hexaene-5,11,15,21-tetrone

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)OCC34C2=C1C(=O)CC3(O)C1C(O)C42COC(=O)C3=C(O)C(Cl)=C(C)C(C1=O)=C23

InChI Identifier

InChI=1S/C26H19ClO10/c1-7-3-9(28)13-16-11(7)10(29)4-26(35)17-19(30)12-8(2)18(27)20(31)14-15(12)24(21(17)32,5-36-23(14)34)25(16,26)6-37-22(13)33/h3,17,21,28,31-32,35H,4-6H2,1-2H3

InChI Key

YNFQXIDQMWVTNH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gilmaniella humicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Benzopyran
Isochromane
2-benzopyran
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Aryl chloride
Aryl halide
Dicarboxylic acid or derivatives
Cyclic alcohol
Vinylogous acid
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organohalogen compound
Organochloride
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.27	ALOGPS
logP	2.34	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.61	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	167.66 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	126.32 m³·mol⁻¹	ChemAxon
Polarizability	48.28 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone (NP0206828)

MOL for NP0206828 (18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone)

3D MOL for NP0206828 (18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone)

3D SDF for NP0206828 (18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone)

3D-SDF for NP0206828 (18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone)

PDB for NP0206828 (18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone)

3D PDB for NP0206828 (18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone)

SMILES for NP0206828 (18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone)

INCHI for NP0206828 (18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone)

Structure for NP0206828 (18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone)

3D Structure for NP0206828 (18-chloro-7,13,19,24-tetrahydroxy-9,17-dimethyl-4,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1²,⁶.0²,¹³.0¹⁰,²⁶.0²⁰,²⁵]hexacosa-6,8,10(26),16,18,20(25)-hexaene-5,11,15,21-tetrone)